Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

TY - JOUR

T1 - Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

AU - Hrdlicka, Patrick J

AU - Andersen, Nicolai K

AU - Jepsen, Jan S

AU - Hansen, Flemming G

AU - Haselmann, Kim F

AU - Nielsen, Claus

AU - Wengel, Jesper

AU - Stenvang, Jan

PY - 2005/4/1

Y1 - 2005/4/1

N2 - The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.

AB - The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.

KW - Anti-HIV Agents

KW - Antineoplastic Agents

KW - Cell Line

KW - Cell Line, Tumor

KW - Cell Survival

KW - Crystallography, X-Ray

KW - Cytidine

KW - Humans

KW - Models, Molecular

KW - Molecular Mimicry

KW - Nucleic Acid Conformation

KW - Uridine

U2 - 10.1016/j.bmc.2005.01.029

DO - 10.1016/j.bmc.2005.01.029

M3 - Journal article

C2 - 15755661

SN - 0968-0896

VL - 13

SP - 2597

EP - 2621

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 7

ER -